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| Name | Liothyronine | ||||||||||||||||||||||||||||||||||||||||||
| Accession Number | DB00279 (APRD01074) | ||||||||||||||||||||||||||||||||||||||||||
| Type | small molecule | ||||||||||||||||||||||||||||||||||||||||||
| Groups | approved | ||||||||||||||||||||||||||||||||||||||||||
| Description | The L-triiodothyronine (T3, liothyronine) thyroid hormone is normally synthesized and secreted by the thyroid gland in much smaller quantities than L-tetraiodothyronine (T4, levothyroxine, L-thyroxine). Most T3 is derived from peripheral monodeiodination of T4 at the 5 position of the outer ring of the iodothyronine nucleus. The hormone finally delivered and used by the tissues is mainly T3. [PubChem] |
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| Structure |
Download: MOL | SDF | SMILES | InChI Display: 2D Structure | 3D Structure |
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| Salts | Not Available | ||||||||||||||||||||||||||||||||||||||||||
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| CAS number | 6893-02-3 | ||||||||||||||||||||||||||||||||||||||||||
| Weight |
Average: 650.9735 Monoisotopic: 650.790038137 |
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| Chemical Formula | C15H12I3NO4 | ||||||||||||||||||||||||||||||||||||||||||
| InChI Key | InChIKey=AUYYCJSJGJYCDS-LBPRGKRZSA-N | ||||||||||||||||||||||||||||||||||||||||||
| InChI |
InChI=1S/C15H12I3NO4/c16-9-6-8(1-2-13(9)20)23-14-10(17)3-7(4-11(14)18)5-12(19)15(21)22/h1-4,6,12,20H,5,19H2,(H,21,22)/t12-/m0/s1
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| IUPAC Name |
(2S)-2-amino-3-[4-(4-hydroxy-3-iodophenoxy)-3,5-diiodophenyl]propanoic acid
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| SMILES |
N[C@@H](CC1=CC(I)=C(OC2=CC(I)=C(O)C=C2)C(I)=C1)C(O)=O
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| Mass Spec | Not Available | ||||||||||||||||||||||||||||||||||||||||||
| Taxonomy | |||||||||||||||||||||||||||||||||||||||||||
| Kingdom | Organic | ||||||||||||||||||||||||||||||||||||||||||
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| Pharmacology | |||||||||||||||||||||||||||||||||||||||||||
| Indication | Used as replacement or supplemental therapy in patients with hypothyroidism of any etiology, except transient hypothyrodism during the recovery phase of subacute thyroiditis. | ||||||||||||||||||||||||||||||||||||||||||
| Pharmacodynamics | Thyroid hormone drugs are natural or synthetic preparations containing T4 or T3 or both. T4 and T3 are produced in the human thyroid gland by the iodination and coupling of the amino acid tyrosine. Liothyronine (T3) contains three atoms of iodine and is formed by the coupling of one molecule of diiodotyrosine (DIT) with one molecule of monoiodotyrosine (MIT). These hormones enhance oxygen consumption by most tissues of the body and increase the basal metabolic rate and the metabolism of carbohydrates, lipids and proteins. Thus, they exert a profound influence on every organ system in the body and are of particular importance in the development of the central nervous system. | ||||||||||||||||||||||||||||||||||||||||||
| Mechanism of action | The hormones, T4 and T3, are tyrosine-based hormones produced by the thyroid gland. Iodine is an important component in their synthesis. The major form of thyroid hormone in the blood is thyroxine (T4). This is converted to the more active liothyronine form by deiodinases in peripheral tissues. Liothyronine acts on the body to increase the basal metabolic rate, affect protein synthesis and increase the body's sensitivity to catecholamines (such as adrenaline). The thyroid hormones are essential to proper development and differentiation of all cells of the human body. To various extents T4 and T3 regulate protein, fat and carbohydrate metabolism. Their most pronounced effect is on how human cells use energetic compounds. The thyroid hormone derivatives bind to the thyroid hormone receptors initially to initiate their downstream effects. | ||||||||||||||||||||||||||||||||||||||||||
| Absorption | 95% in 4 hours | ||||||||||||||||||||||||||||||||||||||||||
| Volume of distribution | Not Available | ||||||||||||||||||||||||||||||||||||||||||
| Protein binding | 99.7% | ||||||||||||||||||||||||||||||||||||||||||
| Metabolism | Not Available | ||||||||||||||||||||||||||||||||||||||||||
| Route of elimination | Not Available | ||||||||||||||||||||||||||||||||||||||||||
| Half life | 2.5 days | ||||||||||||||||||||||||||||||||||||||||||
| Clearance | Not Available | ||||||||||||||||||||||||||||||||||||||||||
| Toxicity | Not Available | ||||||||||||||||||||||||||||||||||||||||||
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| Pathways | Not Available | ||||||||||||||||||||||||||||||||||||||||||
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| Prices |
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational
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| Patents | Not Available | ||||||||||||||||||||||||||||||||||||||||||
| Properties | |||||||||||||||||||||||||||||||||||||||||||
| State | solid | ||||||||||||||||||||||||||||||||||||||||||
| Experimental Properties |
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| Synthesis Reference | Not Available | ||||||||||||||||||||||||||||||||||||||||||
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| PDB Entries | Not Available | ||||||||||||||||||||||||||||||||||||||||||
| FDA label | show (40.8 KB) | ||||||||||||||||||||||||||||||||||||||||||
| MSDS | show (73.4 KB) | ||||||||||||||||||||||||||||||||||||||||||
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| Food Interactions | Not Available | ||||||||||||||||||||||||||||||||||||||||||
| Targets |
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1. Thyroid hormone receptor alpha Pharmacological action: yesActions: agonist Nuclear hormone receptor. High affinity receptor for triiodothyronine Organism class: humanUniProt ID: P10827 ![]() Gene: THRA ![]() Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report ![]() References:
2. Thyroid hormone receptor beta-1 Pharmacological action: yesActions: agonist High affinity receptor for triiodothyronine Organism class: humanUniProt ID: P10828 ![]() Gene: THRB ![]() Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report ![]() References:
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| Transporters |
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1. Solute carrier organic anion transporter family member 1A2 Actions: substrateMediates the Na(+)-independent transport of organic anions such as sulfobromophthalein (BSP) and conjugated (taurocholate) and unconjugated (cholate) bile acids (By similarity) UniProt ID: P46721![]() Gene: SLCO1A2 ![]() Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report ![]() References:
2. Solute carrier organic anion transporter family member 1B1 Actions: substrateMediates the Na(+)-independent transport of organic anions such as pravastatin, taurocholate, methotrexate, dehydroepiandrosterone sulfate, 17-beta-glucuronosyl estradiol, estrone sulfate, prostaglandin E2, thromboxane B2, leukotriene C3, leukotriene E4, thyroxine and triiodothyronine. May play an important role in the clearance of bile acids and organic anions from the liver UniProt ID: Q9Y6L6![]() Gene: SLCO1B1 ![]() Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report ![]() References:
3. Solute carrier organic anion transporter family member 1B3 Actions: substrateMediates the Na(+)-independent transport of organic anions such as 17-beta-glucuronosyl estradiol, taurocholate, triiodothyronine (T3), leukotriene C4, dehydroepiandrosterone sulfate (DHEAS), methotrexate and sulfobromophthalein (BSP) UniProt ID: Q9NPD5![]() Gene: SLCO1B3 ![]() Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report ![]() References:
4. Solute carrier organic anion transporter family member 4C1 Actions: substrateOrganic anion transporter, capable of transporting pharmacological substances such as digoxin, ouabain, thyroxine, methotrexate and cAMP. May participate in the regulation of membrane transport of ouabain. Involved in the uptake of the dipeptidyl peptidase-4 inhibitor sitagliptin and hence may play a role in its transport into and out of renal proximal tubule cells. May be involved in the first step of the transport pathway of digoxin and various compounds into the urine in the kidney. May be involved in sperm maturation by enabling directed movement of organic anions and compounds within or between cells. This ion- transporting process is important to maintain the strict epididymal homeostasis necessary for sperm maturation. May have a role in secretory functions since seminal vesicle epithelial cells are assumed to secrete proteins involved in decapacitation by modifying surface proteins to facilitate the acquisition of the ability to fertilize the egg UniProt ID: Q6ZQN7![]() Gene: SLCO4C1 ![]() Protein Sequence: FASTA SNPs: SNPJam Report ![]() References:
5. Sodium/bile acid cotransporter Actions: substrateThe hepatic sodium/bile acid uptake system exhibits broad substrate specificity and transports various non-bile acid organic compounds as well. It is strictly dependent on the extracellular presence of sodium UniProt ID: Q14973![]() Gene: SLC10A1 ![]() Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report ![]() References:
6. Solute carrier organic anion transporter family member 1C1 Actions: substrate, inhibitorMediates the Na(+)-independent high affinity transport of organic anions such as the thyroid hormones thyroxine (T4) and rT3. Other potential substrates, such as triiodothyronine (T3), 17-beta-glucuronosyl estradiol, estrone-3-sulfate and sulfobromophthalein (BSP) are transported with much lower efficiency UniProt ID: Q9NYB5![]() Gene: SLCO1C1 ![]() Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report ![]() References:
7. Solute carrier organic anion transporter family member 4A1 Actions: substrate, inhibitorMediates the Na(+)-independent transport of organic anions such as the thyroid hormones T3 (triiodo-L-thyronine), T4 (thyroxine) and rT3, and of estrone-3-sulfate and taurocholate UniProt ID: Q96BD0![]() Gene: SLCO4A1 ![]() Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report ![]() References:
8. Solute carrier family 22 member 8 Actions: inhibitorPlays an important role in the excretion/detoxification of endogenous and exogenous organic anions, especially from the brain and kidney. Involved in the transport basolateral of steviol, fexofenadine. Transports benzylpenicillin (PCG), estrone- 3-sulfate (E1S), cimetidine (CMD), 2,4-dichloro-phenoxyacetate (2,4-D), p-amino-hippurate (PAH), acyclovir (ACV) and ochratoxin (OTA) UniProt ID: Q8TCC7![]() Gene: SLC22A8 ![]() Protein Sequence: FASTA SNPs: SNPJam Report ![]() References:
9. Monocarboxylate transporter 10 Actions: inhibitorSodium-independent transporter that mediates the update of aromatic acid. Can function as a net efflux pathway for aromatic amino acids in the basosolateral epithelial cells (By similarity) UniProt ID: Q8TF71![]() Gene: SLC16A10 ![]() Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report ![]() References:
10. Multidrug resistance protein 1 Actions: inducerEnergy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells UniProt ID: P08183![]() Gene: ABCB1 ![]() Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report ![]() References:
11. Large neutral amino acids transporter small subunit 1 Sodium-independent, high-affinity transport of large neutral amino acids. Involved in cellular amino acid uptake UniProt ID: Q01650![]() Gene: SLC7A5 ![]() Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report ![]() References:
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| Carriers |
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Thyroid hormone-binding protein. Probably transports thyroxine from the bloodstream to the brain UniProt ID: P02766![]() Gene: TTR ![]() Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report ![]() References:
Major thyroid hormone transport protein in serum UniProt ID: P05543![]() Gene: SERPINA7 ![]() Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report ![]() References:
Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloidal osmotic pressure of blood UniProt ID: P02768![]() Gene: ALB ![]() Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report ![]() References:
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